Don't the small Smarts, including the Roadster, have a rather nasty reputation for blowing engines early doors?
Shame that practical wasn't a factor and good looks was[1]. I'd have suggested a ForFour. I had one as a courtesy car recently and it was exactly like driving a big Go-Kart. Oodles of fun, once I worked out that that Mitsu engine rewards you in spades for caning the living wotsits off it. I think they include a free cheesy grin with each car.
As it was getting on a bit, a garage courtesy car and had probably been thrashed within an inch of its life every day, I guess they're reliable too...;-)
[1] Then again, I quite like 'em. I can see that some wouldn't though.
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